CA2192965C - Compositions d'analogues d'anandamide et procede de traitement de l'hypertension intra-oculaire a l'aide de telles compositions - Google Patents
Compositions d'analogues d'anandamide et procede de traitement de l'hypertension intra-oculaire a l'aide de telles compositions Download PDFInfo
- Publication number
- CA2192965C CA2192965C CA002192965A CA2192965A CA2192965C CA 2192965 C CA2192965 C CA 2192965C CA 002192965 A CA002192965 A CA 002192965A CA 2192965 A CA2192965 A CA 2192965A CA 2192965 C CA2192965 C CA 2192965C
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- Prior art keywords
- integer
- arachidonyl
- ophthalmic composition
- heterocyclic ring
- ident
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 55
- LGEQQWMQCRIYKG-DOFZRALJSA-N anandamide Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO LGEQQWMQCRIYKG-DOFZRALJSA-N 0.000 title claims abstract description 39
- 206010020772 Hypertension Diseases 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title abstract description 7
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 64
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 230000004410 intraocular pressure Effects 0.000 claims description 166
- 239000000243 solution Substances 0.000 claims description 152
- 125000004097 arachidonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 116
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- LGEQQWMQCRIYKG-UHFFFAOYSA-N arachidonic acid ethanolamide Natural products CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO LGEQQWMQCRIYKG-UHFFFAOYSA-N 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- JLICLHRHKNFLOO-ZKWNWVNESA-N CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCNC(C)=O Chemical compound CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCNC(C)=O JLICLHRHKNFLOO-ZKWNWVNESA-N 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 125000002837 carbocyclic group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
- RRRUFIJYUHYHGE-DOFZRALJSA-N CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCN Chemical compound CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCN RRRUFIJYUHYHGE-DOFZRALJSA-N 0.000 claims description 12
- -1 2-hydroxypropyl- Chemical group 0.000 claims description 11
- RZXHODDKSJVFHT-DOFZRALJSA-N n-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenyl]morpholine-4-carboxamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCNC(=O)N1CCOCC1 RZXHODDKSJVFHT-DOFZRALJSA-N 0.000 claims description 11
- 239000006172 buffering agent Substances 0.000 claims description 10
- 230000002708 enhancing effect Effects 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229920003169 water-soluble polymer Polymers 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 229920002674 hyaluronan Polymers 0.000 claims description 3
- 229960003160 hyaluronic acid Drugs 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 3
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 235000010981 methylcellulose Nutrition 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 3
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 3
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 238000011260 co-administration Methods 0.000 claims 2
- 229940031576 hydroxypropylbetadex (0.58-0.68 ms) Drugs 0.000 claims 2
- 229920006316 polyvinylpyrrolidine Polymers 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 28
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 254
- 241000283973 Oryctolagus cuniculus Species 0.000 description 202
- 239000011780 sodium chloride Substances 0.000 description 127
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 238000005259 measurement Methods 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
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- 210000004087 cornea Anatomy 0.000 description 19
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- CMHHMUWAYWTMGS-UHFFFAOYSA-N oxybuprocaine Chemical compound CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N CMHHMUWAYWTMGS-UHFFFAOYSA-N 0.000 description 18
- 229960003502 oxybuprocaine Drugs 0.000 description 18
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- 230000001631 hypertensive effect Effects 0.000 description 16
- 230000003444 anaesthetic effect Effects 0.000 description 14
- GVUKBGNMKOQPKH-ZKWNWVNESA-N CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCOC Chemical compound CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCOC GVUKBGNMKOQPKH-ZKWNWVNESA-N 0.000 description 11
- XEFRYSYSOVYIFV-DOFZRALJSA-N CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCF Chemical compound CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCNCCF XEFRYSYSOVYIFV-DOFZRALJSA-N 0.000 description 9
- 229940097362 cyclodextrins Drugs 0.000 description 8
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- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 6
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 6
- 229960004242 dronabinol Drugs 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 244000025254 Cannabis sativa Species 0.000 description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
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- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- 102100025074 C-C chemokine receptor-like 2 Human genes 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 1
- 108050007331 Cannabinoid receptor Proteins 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- XXGMIHXASFDFSM-UHFFFAOYSA-N Delta9-tetrahydrocannabinol Natural products CCCCCc1cc2OC(C)(C)C3CCC(=CC3c2c(O)c1O)C XXGMIHXASFDFSM-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101000716068 Homo sapiens C-C chemokine receptor type 6 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- FPVRUILUEYSIMD-RPRRAYFGSA-N [(8s,9r,10s,11s,13s,14s,16r,17r)-9-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(OC(C)=O)[C@@]1(C)C[C@@H]2O FPVRUILUEYSIMD-RPRRAYFGSA-N 0.000 description 1
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- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
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- 229960003957 dexamethasone Drugs 0.000 description 1
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- LNGNZSMIUVQZOX-UHFFFAOYSA-L disodium;dioxido(sulfanylidene)-$l^{4}-sulfane Chemical compound [Na+].[Na+].[O-]S([O-])=S LNGNZSMIUVQZOX-UHFFFAOYSA-L 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- Health & Medical Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
L'invention concerne des analogues d'anandamide destinés à être utilisés pour le traitement de l'hypertension intra-oculaire, des compositions ophthalmiques comprenant lesdits analogues d'anandamide et une cyclodextrine ainsi que des procédés de traitement de l'hypertension intra-oculaire à l'aide de ces composés.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/272,532 | 1994-07-11 | ||
| US08/272,532 US5631297A (en) | 1994-07-11 | 1994-07-11 | Anandamides useful for the treatment of intraocular hypertension, ophthalmic compositions containing the same and methods of use of the same |
| US45744295A | 1995-06-01 | 1995-06-01 | |
| US08/457,442 | 1995-06-01 | ||
| PCT/US1995/008226 WO1996001558A1 (fr) | 1994-07-11 | 1995-07-10 | Compositions d'analogues d'anandamide et procede de traitement de l'hypertension intra-oculaire a l'aide de telles compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2192965A1 CA2192965A1 (fr) | 1996-01-25 |
| CA2192965C true CA2192965C (fr) | 2007-12-04 |
Family
ID=26955582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002192965A Expired - Fee Related CA2192965C (fr) | 1994-07-11 | 1995-07-10 | Compositions d'analogues d'anandamide et procede de traitement de l'hypertension intra-oculaire a l'aide de telles compositions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5977180A (fr) |
| EP (1) | EP0777415A4 (fr) |
| AU (1) | AU3124995A (fr) |
| CA (1) | CA2192965C (fr) |
| WO (1) | WO1996001558A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI109087B (fi) * | 1998-12-23 | 2002-05-31 | Tomi Jaervinen | Menetelmä farmaseuttisen koostumuksen valmistamiseksi |
| CA2410401A1 (fr) * | 2000-05-23 | 2001-11-29 | Daniele Piomelli | Nouveau traitement contre la toux |
| WO2003097573A1 (fr) * | 2002-05-16 | 2003-11-27 | Sepracor, Inc. | Amines inhibant un transporteur d'anandamide de type mammalien, et procedes d'utilisation |
| JP2009538827A (ja) * | 2006-05-01 | 2009-11-12 | イースタン バージニア メディカル スクール | カンナビノイドおよび使用方法 |
| BR112012031194A2 (pt) * | 2010-06-08 | 2018-05-29 | Krisani Biosciences P Ltd | derivados de cisteamina e seu uso no tratamento de ehna |
| CN109419789B (zh) * | 2017-08-31 | 2021-09-21 | 清华大学 | 治疗和/或预防免疫紊乱疾病的化合物及其应用 |
| IT201700120375A1 (it) * | 2017-10-24 | 2019-04-24 | For Health Pharma S R L | Soluzioni acquose stabili che comprendono PUFAs |
| US20250205181A1 (en) * | 2021-08-04 | 2025-06-26 | Czap Research And Development, Llc | Anandamide cyclodextrin inclusion complex vehicles |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3649650A (en) * | 1970-02-13 | 1972-03-14 | Little Inc A | Novel derivatives of tetrahydro-cannabinol |
| US4327028A (en) * | 1978-08-17 | 1982-04-27 | Calcol, Inc. | Composition of matter |
| JPS58126810A (ja) * | 1981-12-24 | 1983-07-28 | Kaken Pharmaceut Co Ltd | 抗炎症眼科用液剤およびその製法 |
| US4476140A (en) * | 1983-05-16 | 1984-10-09 | Yale University | Composition and method for treatment of glaucoma |
| US5002935A (en) * | 1987-12-30 | 1991-03-26 | University Of Florida | Improvements in redox systems for brain-targeted drug delivery |
| ES2037385T3 (es) * | 1988-01-14 | 1993-06-16 | Akzo N.V. | Un procedimiento de manufactura de una preparacion farmaceutica para administracion local. |
| CA1321192C (fr) * | 1988-04-20 | 1993-08-10 | Abdul Majid | Complexes d'inclusion de cyclodextrines obtenus par agglomeration |
| CA2017156A1 (fr) * | 1989-06-02 | 1990-12-02 | Sotoo Asakura | Preparation de la substance fr115224 pour administration parenterale |
| CA2031469A1 (fr) * | 1989-12-28 | 1991-06-29 | Larry A. Wheeler | Utilisation de composes d'inclusion de prostaglandines avec des cyclodextrines dans le traitement de l'hypertension oculaire |
| TW200402B (fr) * | 1990-08-13 | 1993-02-21 | Senju Pharma Co | |
| IL103932A (en) * | 1992-11-30 | 1997-02-18 | Yissum Res & Dev | Fatty acid and pharmaceutical compositions containing them |
| SE501482C2 (sv) * | 1993-06-24 | 1995-02-27 | Leiras Oy | Komposition för topisk administration av bispilokarpinsyradiestrar till ögat i form av en vattenlösning |
| US5631297A (en) * | 1994-07-11 | 1997-05-20 | Pate; David W. | Anandamides useful for the treatment of intraocular hypertension, ophthalmic compositions containing the same and methods of use of the same |
-
1995
- 1995-07-10 CA CA002192965A patent/CA2192965C/fr not_active Expired - Fee Related
- 1995-07-10 US US08/776,268 patent/US5977180A/en not_active Expired - Lifetime
- 1995-07-10 AU AU31249/95A patent/AU3124995A/en not_active Abandoned
- 1995-07-10 WO PCT/US1995/008226 patent/WO1996001558A1/fr not_active Ceased
- 1995-07-10 EP EP95927121A patent/EP0777415A4/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0777415A1 (fr) | 1997-06-11 |
| AU3124995A (en) | 1996-02-09 |
| EP0777415A4 (fr) | 1999-06-16 |
| CA2192965A1 (fr) | 1996-01-25 |
| US5977180A (en) | 1999-11-02 |
| WO1996001558A1 (fr) | 1996-01-25 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |